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1205 Eagle Pond Drive Unit 1205, Winter Haven

Enjoy the Florida lifestyle in Cypresswood Golf & Country Club! This inviting 2-bedroom, 2-bathroom second-floor condo offers comfortable living in a desirable Winter Haven community. PRICED TO SELL. The home features LVP flooring, a newer water heater, and convenient exterior storage for golf equipment, seasonal items, and more. Cypresswood Golf & Country Club offers an array of amenities, including a 24-hour manned guard gate, an 18-hole championship golf course, tennis, pickleball and basketball courts, community pool, restaurant, clubhouse and more. Whether you're looking for a full-time residence, winter retreat, or a place to enjoy an active Florida lifestyle, this condo offers comfort and convenience in a welcoming community. Conveniently located near US-27, you'll have easy access to restaurants, shopping, entertainment, and everyday conveniences, while still enjoying the relaxed atmosphere of a golf and country club community. Low monthly HOA fee. Schedule your visit TODAY.

2 Beds ⋅ 2 Baths ⋅ S5158253 MLS ⋅ 1205 BLDG.

Enjoy the Florida lifestyle in Cypresswood Golf & Country Club! This inviting 2-bedroom, 2-bathroom second-floor condo offers comfortable living in a desirable Winter Haven community. PRICED TO SELL. The home features LVP flooring, a newer water heater, and convenient exterior storage for golf equipment, seasonal items, and more. Cypresswood Golf & Country Club offers an array of amenities, including a 24-hour manned guard gate, an 18-hole championship golf course, tennis, pickleball and basketball courts, community pool, restaurant, clubhouse and more. Whether you're looking for a full-time residence, winter retreat, or a place to enjoy an active Florida lifestyle, this condo offers comfort and convenience in a welcoming community. Conveniently located near US-27, you'll have easy access to restaurants, shopping, entertainment, and everyday conveniences, while still enjoying the relaxed atmosphere of a golf and country club community. Low monthly HOA fee. Schedule your visit TODAY.

1205 Eagle Pond Drive Unit 1205, Winter Haven

Listing courtesy of FLORIDA SPIRIT HOMES. 407-396-4441

$295,000

Virtually Staged. Weclome to this move-in ready single story home with a bright, open floor plan and inviting living spaces. The spacious kitchen features granite countertops, stainless steel appliances, and ample cabinet space. Functional vinyl flooring enhances the main living areas, while spacious bedrooms provide comfortable accommodations. An attached two car garage adds convenience to this lovely home. Easy to show!

4 Beds ⋅ 2 Baths ⋅ C7531097 MLS

Virtually Staged. Weclome to this move-in ready single story home with a bright, open floor plan and inviting living spaces. The spacious kitchen features granite countertops, stainless steel appliances, and ample cabinet space. Functional vinyl flooring enhances the main living areas, while spacious bedrooms provide comfortable accommodations. An attached two car garage adds convenience to this lovely home. Easy to show!

4750 Osprey Way, Winter Haven

Listing courtesy of SOVEREIGN REAL ESTATE GROUP. 305-662-1502

$319,900

SINGLE-FAMILY HOME WITH DETACHED IN-LAW SUITE, RENTAL INCOME & NO HOA! This unique Winter Haven property features a 3-BEDROOM, 1-BATH MAIN HOME plus a separate 1-BEDROOM, 1-BATH DETACHED IN-LAW SUITE, ideal for MULTIGENERATIONAL LIVING, extended family, guests, or ADDITIONAL RENTAL INCOME. The main home is currently operated as a SHORT-TERM RENTAL and is being sold FULLY FURNISHED, with furniture included in the sale price, offering a TURNKEY opportunity for a new owner or a MOVE-IN-READY PRIMARY RESIDENCE. The detached suite has its own PRIVATE ENTRANCE, SEPARATE ADDRESS, PARKING, and SEPARATE UTILITIES currently paid by the tenant, and is generating $1,095/MONTH in rental income while maintaining privacy between both living spaces. Major improvements include NEWER ROOFS completed within approximately the last two years, UPDATED PLUMBING, and CENTRAL A/C for both living spaces. Located just minutes from DOWNTOWN WINTER HAVEN with convenient access to restaurants, shopping, entertainment, and the continued GROWTH AND DEVELOPMENT happening throughout the area. Live in the main home while collecting rental income, continue utilizing the main home as a SHORT-TERM RENTAL, or accommodate extended family—the property offers exceptional FLEXIBILITY for a variety of living arrangements and income opportunities, subject to applicable local regulations. NO HOA!

4 Beds ⋅ 2 Baths ⋅ O6443878 MLS

SINGLE-FAMILY HOME WITH DETACHED IN-LAW SUITE, RENTAL INCOME & NO HOA! This unique Winter Haven property features a 3-BEDROOM, 1-BATH MAIN HOME plus a separate 1-BEDROOM, 1-BATH DETACHED IN-LAW SUITE, ideal for MULTIGENERATIONAL LIVING, extended family, guests, or ADDITIONAL RENTAL INCOME. The main home is currently operated as a SHORT-TERM RENTAL and is being sold FULLY FURNISHED, with furniture included in the sale price, offering a TURNKEY opportunity for a new owner or a MOVE-IN-READY PRIMARY RESIDENCE. The detached suite has its own PRIVATE ENTRANCE, SEPARATE ADDRESS, PARKING, and SEPARATE UTILITIES currently paid by the tenant, and is generating $1,095/MONTH in rental income while maintaining privacy between both living spaces. Major improvements include NEWER ROOFS completed within approximately the last two years, UPDATED PLUMBING, and CENTRAL A/C for both living spaces. Located just minutes from DOWNTOWN WINTER HAVEN with convenient access to restaurants, shopping, entertainment, and the continued GROWTH AND DEVELOPMENT happening throughout the area. Live in the main home while collecting rental income, continue utilizing the main home as a SHORT-TERM RENTAL, or accommodate extended family—the property offers exceptional FLEXIBILITY for a variety of living arrangements and income opportunities, subject to applicable local regulations. NO HOA!

113 Avenue C Se, Winter Haven

Listing courtesy of LPT REALTY, LLC. 877-366-2213

$275,000

Perfect for a family purchasing their first home! This four-bedroom, two-bath home offers comfortable Florida living with a functional layout and great outdoor space. One of the standout features is the private, fully fenced backyard, along with a screened-in back patio and covered lanai that create the perfect setting for relaxing, entertaining, or enjoying your morning coffee. Luxury vinyl plank (LVP) flooring runs throughout all bedrooms and main living areas, creating a clean, updated, and easy-to-maintain look, while the bathrooms feature tile flooring. All appliances convey with the home, including the washer, dryer, refrigerator, stove, and garbage disposal, making this home even more move-in ready. The combination of the screened patio, covered lanai, and fenced yard provides an excellent extension of the home’s living space and added privacy. Conveniently located in Winter Haven with access to shopping, dining, entertainment, and major roadways, this home offers a great combination of indoor comfort, outdoor living, and everyday convenience. Schedule your private showing today and see everything this home has to offer!

4 Beds ⋅ 2 Baths ⋅ G5118159 MLS

Perfect for a family purchasing their first home! This four-bedroom, two-bath home offers comfortable Florida living with a functional layout and great outdoor space. One of the standout features is the private, fully fenced backyard, along with a screened-in back patio and covered lanai that create the perfect setting for relaxing, entertaining, or enjoying your morning coffee. Luxury vinyl plank (LVP) flooring runs throughout all bedrooms and main living areas, creating a clean, updated, and easy-to-maintain look, while the bathrooms feature tile flooring. All appliances convey with the home, including the washer, dryer, refrigerator, stove, and garbage disposal, making this home even more move-in ready. The combination of the screened patio, covered lanai, and fenced yard provides an excellent extension of the home’s living space and added privacy. Conveniently located in Winter Haven with access to shopping, dining, entertainment, and major roadways, this home offers a great combination of indoor comfort, outdoor living, and everyday convenience. Schedule your private showing today and see everything this home has to offer!

255 Haines Boulevard, Winter Haven

Listing courtesy of PREFERRED RE BROKERS III. 407-440-4900

$258,000

Welcome to 824 Vienna Dr, a beautiful Well sought out community 3-bedroom, 2-bathroom home located in the desirable Villamar Phase 1 community of Winter Haven! Built in 2021, this well-maintained home offers approximately 1,402 square feet of comfortable living space with a spacious open-concept design that makes everyday living and entertaining effortless. Step inside to a bright and inviting living area that flows naturally into the dining space and kitchen, creating a comfortable gathering place for family and friends. The primary suite offers a private retreat with its own bathroom, while two additional bedrooms provide plenty of space for family, guests, a home office, or hobbies. A 2-car attached garage adds convenience and valuable storage space. One of the standout features of this property is the larger lot, giving you more room to enjoy the outdoors and create the backyard you've always wanted. The possibilities are endless from adding a pool or playground to creating an outdoor entertaining area, garden, fire-pit space, or your own private backyard oasis, subject to applicable HOA and local requirements. Community itself has a playground, park, and large resort style pool. Located in Villamar Phase 1, you'll enjoy a welcoming community atmosphere with convenient access to shopping, dining, schools, parks, major roadways, and everything Winter Haven has to display. Whether you're looking for your first home, a place to grow your family, or a newer property with room to make it your own, 824 Vienna Dr is an opportunity you won't want to miss. Schedule your private showing today!

3 Beds ⋅ 2 Baths ⋅ O6443270 MLS

Welcome to 824 Vienna Dr, a beautiful Well sought out community 3-bedroom, 2-bathroom home located in the desirable Villamar Phase 1 community of Winter Haven! Built in 2021, this well-maintained home offers approximately 1,402 square feet of comfortable living space with a spacious open-concept design that makes everyday living and entertaining effortless. Step inside to a bright and inviting living area that flows naturally into the dining space and kitchen, creating a comfortable gathering place for family and friends. The primary suite offers a private retreat with its own bathroom, while two additional bedrooms provide plenty of space for family, guests, a home office, or hobbies. A 2-car attached garage adds convenience and valuable storage space. One of the standout features of this property is the larger lot, giving you more room to enjoy the outdoors and create the backyard you've always wanted. The possibilities are endless from adding a pool or playground to creating an outdoor entertaining area, garden, fire-pit space, or your own private backyard oasis, subject to applicable HOA and local requirements. Community itself has a playground, park, and large resort style pool. Located in Villamar Phase 1, you'll enjoy a welcoming community atmosphere with convenient access to shopping, dining, schools, parks, major roadways, and everything Winter Haven has to display. Whether you're looking for your first home, a place to grow your family, or a newer property with room to make it your own, 824 Vienna Dr is an opportunity you won't want to miss. Schedule your private showing today!

824 Vienna Drive, Winter Haven

Listing courtesy of DALTON WADE INC. 888-668-8283

$174,500

5 BEDROOMS + FLEX SPACE! Discover an impressive amount of space and versatility in this 5-bedroom, 2-bath manufactured home. In addition to five bedrooms, a dedicated flex room provides even more functionality—ideal for a home office, hobby room, playroom, or additional living space. Inside, you'll find several updates, including refreshed bathrooms, a tiled shower, updated flooring in key areas, and fresh interior paint. The kitchen flows into the dining area and features additional counter seating, providing a functional layout for everyday living and entertaining. Outside, the 0.21-acre lot offers usable yard space for gardening, outdoor seating, recreation, or entertaining. Conveniently located in the Wahneta area of Winter Haven, the property is near Wahneta Elementary School and just minutes from Lake Gwyn Park, with walking trails, sports fields, playgrounds, and a screened pavilion. With its flexible layout, recent interior updates, usable outdoor space, and convenient Winter Haven location, this property offers plenty of possibilities as a primary residence or investment opportunity. Schedule your showing today!

5 Beds ⋅ 2 Baths ⋅ TB8551383 MLS

5 BEDROOMS + FLEX SPACE! Discover an impressive amount of space and versatility in this 5-bedroom, 2-bath manufactured home. In addition to five bedrooms, a dedicated flex room provides even more functionality—ideal for a home office, hobby room, playroom, or additional living space. Inside, you'll find several updates, including refreshed bathrooms, a tiled shower, updated flooring in key areas, and fresh interior paint. The kitchen flows into the dining area and features additional counter seating, providing a functional layout for everyday living and entertaining. Outside, the 0.21-acre lot offers usable yard space for gardening, outdoor seating, recreation, or entertaining. Conveniently located in the Wahneta area of Winter Haven, the property is near Wahneta Elementary School and just minutes from Lake Gwyn Park, with walking trails, sports fields, playgrounds, and a screened pavilion. With its flexible layout, recent interior updates, usable outdoor space, and convenient Winter Haven location, this property offers plenty of possibilities as a primary residence or investment opportunity. Schedule your showing today!

306 Avenue A Wahneta E, Winter Haven

Listing courtesy of PREFERRED SHORE LLC. 941-999-1179

1100 Martinique Drive Unit 220, Winter Haven

$149,900

Welcome to easy Florida living in the desirable community of Orchid Springs! This beautifully updated second-floor CORNER/END-UNIT condo offers a wonderful sense of privacy along with an abundance of natural light. Featuring a spacious, open split-bedroom floor plan with 3 bedrooms, 2 bathrooms, an enclosed bonus room and a dedicated inside laundry room, this modern-looking unit provides plenty of comfortable & flexible living space. Thoughtful updates and custom touches can be found throughout, including crown molding and stylish finishes. The beautiful kitchen features granite countertops, updated stainless steel appliances and plenty of cabinet and counter space, creating a functional and inviting space for everyday living and entertaining. The spacious primary suite offers a walk-in closet and private ensuite bathroom with a step-in shower and granite countertop. The split-bedroom layout provides added privacy for family or guests, while the enclosed bonus room adds valuable additional living space and can easily serve as a home office, den, hobby room or additional sitting area. Additional conveniences include a full inside laundry room with washer and dryer included, as well as assigned covered parking. Some of the furniture may also be negotiable, making this an excellent option for buyers looking for an easier transition into their new Florida home. One of the many benefits of Orchid Springs is the affordable condo fee, which includes water, gas, sewer, trash, exterior building maintenance and grounds maintenance, providing for a convenient, low-maintenance lifestyle. Residents also enjoy access to the community clubhouse and swimming pool. Ideally located in SE Winter Haven near Highway 27, this condo provides convenient access to shopping, restaurants, medical facilities, LEGOLAND Florida Resort and everyday necessities. Winter Haven's Central Florida location between Tampa and Orlando also makes it convenient for enjoying everything the region has to offer. Whether you are looking for a full-time residence or a seasonal Florida retreat, this beautifully updated corner unit combines privacy, natural light, modern finishes, additional living space and a convenient location. Schedule your private showing today!

3 Beds ⋅ 2 Baths ⋅ S5158041 MLS ⋅ A BLDG.

Welcome to easy Florida living in the desirable community of Orchid Springs! This beautifully updated second-floor CORNER/END-UNIT condo offers a wonderful sense of privacy along with an abundance of natural light. Featuring a spacious, open split-bedroom floor plan with 3 bedrooms, 2 bathrooms, an enclosed bonus room and a dedicated inside laundry room, this modern-looking unit provides plenty of comfortable & flexible living space. Thoughtful updates and custom touches can be found throughout, including crown molding and stylish finishes. The beautiful kitchen features granite countertops, updated stainless steel appliances and plenty of cabinet and counter space, creating a functional and inviting space for everyday living and entertaining. The spacious primary suite offers a walk-in closet and private ensuite bathroom with a step-in shower and granite countertop. The split-bedroom layout provides added privacy for family or guests, while the enclosed bonus room adds valuable additional living space and can easily serve as a home office, den, hobby room or additional sitting area. Additional conveniences include a full inside laundry room with washer and dryer included, as well as assigned covered parking. Some of the furniture may also be negotiable, making this an excellent option for buyers looking for an easier transition into their new Florida home. One of the many benefits of Orchid Springs is the affordable condo fee, which includes water, gas, sewer, trash, exterior building maintenance and grounds maintenance, providing for a convenient, low-maintenance lifestyle. Residents also enjoy access to the community clubhouse and swimming pool. Ideally located in SE Winter Haven near Highway 27, this condo provides convenient access to shopping, restaurants, medical facilities, LEGOLAND Florida Resort and everyday necessities. Winter Haven's Central Florida location between Tampa and Orlando also makes it convenient for enjoying everything the region has to offer. Whether you are looking for a full-time residence or a seasonal Florida retreat, this beautifully updated corner unit combines privacy, natural light, modern finishes, additional living space and a convenient location. Schedule your private showing today!

1100 Martinique Drive Unit 220, Winter Haven

Listing courtesy of RE/MAX HERITAGE PROFESSIONALS. 863-256-2188

$294,000

Welcome to the beautifully maintained 3-bedroom, 2-bath home with a bonus room in the desirable Planters Walk community of SE Winter Haven! Offering approximately 1,640 square feet of living space on a spacious 8,712-square-foot lot, this home provides comfortable living with plenty of room to enjoy both indoors and out. Step inside to find beautiful wood flooring flowing through the entrance, living room, and dining area, creating a warm and inviting atmosphere. The family room and kitchen feature easy-care tile flooring, while the kitchen offers stainless steel appliances and granite countertops. Granite countertops are also featured in the other wet areas of the interior, adding both style and functionality. The bonus room provides flexible space that can be used as a home office, den, craft room, playroom, or additional living area. Outside, enjoy your fully fenced backyard featuring a deck and gazebo—perfect for relaxing, entertaining guests, enjoying your morning coffee, or creating your own private outdoor retreat. The roof was recently replaced, providing an added benefit for the next homeowner. Another great feature is the exceptionally low HOA fee, with no CDD fees, helping keep the cost of ownership affordable. Located in SE Winter Haven, Planters Walk offers convenient access to shopping, restaurants, grocery stores, medical facilities, schools, and major roadways. The area is also close to Winter Haven's famous Chain of Lakes and is just a short drive from LEGOLAND Florida Resort, making this a great location for both everyday living and enjoying Central Florida attractions. Winter Haven offers plenty of opportunities for outdoor recreation and entertainment, including parks, trails, lakes, downtown restaurants, local shopping, and community events. Nearby attractions include South Lake Howard Nature Park, Trailhead Park Playground, and the vibrant Downtown Winter Haven area with its restaurants, shops, events, and local markets. Sizes and measurements are estimates and are to be verified by buyer and or buyers agent.

3 Beds ⋅ 2 Baths ⋅ L4965243 MLS

Welcome to the beautifully maintained 3-bedroom, 2-bath home with a bonus room in the desirable Planters Walk community of SE Winter Haven! Offering approximately 1,640 square feet of living space on a spacious 8,712-square-foot lot, this home provides comfortable living with plenty of room to enjoy both indoors and out. Step inside to find beautiful wood flooring flowing through the entrance, living room, and dining area, creating a warm and inviting atmosphere. The family room and kitchen feature easy-care tile flooring, while the kitchen offers stainless steel appliances and granite countertops. Granite countertops are also featured in the other wet areas of the interior, adding both style and functionality. The bonus room provides flexible space that can be used as a home office, den, craft room, playroom, or additional living area. Outside, enjoy your fully fenced backyard featuring a deck and gazebo—perfect for relaxing, entertaining guests, enjoying your morning coffee, or creating your own private outdoor retreat. The roof was recently replaced, providing an added benefit for the next homeowner. Another great feature is the exceptionally low HOA fee, with no CDD fees, helping keep the cost of ownership affordable. Located in SE Winter Haven, Planters Walk offers convenient access to shopping, restaurants, grocery stores, medical facilities, schools, and major roadways. The area is also close to Winter Haven's famous Chain of Lakes and is just a short drive from LEGOLAND Florida Resort, making this a great location for both everyday living and enjoying Central Florida attractions. Winter Haven offers plenty of opportunities for outdoor recreation and entertainment, including parks, trails, lakes, downtown restaurants, local shopping, and community events. Nearby attractions include South Lake Howard Nature Park, Trailhead Park Playground, and the vibrant Downtown Winter Haven area with its restaurants, shops, events, and local markets. Sizes and measurements are estimates and are to be verified by buyer and or buyers agent.

12 Saint Kitts Circle, Winter Haven

Listing courtesy of LA ROSA REALTY PRESTIGE. 863-940-4850

6624 Winterset Gardens Road, Winter Haven

$450,000

Welcome to 6624 Winterset Gardens Road - this is an ideal home or rental property for those seeking an updated living space with community boat ramp with Chain of Lakes access. This renovated home has 5 bedrooms with 2.5 bathrooms. The renovations include new kitchen cabinets, kitchen appliances and Quartz countertops, fully renovated bathrooms, new flooring, new lighting, new ceiling fans and more. NEW Roof in 2022 and a New Termite bond in 2026! This home also has a newly painted interior/exterior. Winterset Gardens is a highly respected, quaint neighborhood on the shore of Little lake Winterset and offers an optional $100 HOA with a community boat ramp and no deed restrictions allowing direct access to The world renowned Winter Haven Chain of Lakes. 24 canal connected lakes offering great fishing, skiing and leisure boating. Hop on your boat from your neighborhood and go get a bite to eat at several float up bars and restaurants.

5 Beds ⋅ 3 Baths ⋅ O6443972 MLS

Welcome to 6624 Winterset Gardens Road - this is an ideal home or rental property for those seeking an updated living space with community boat ramp with Chain of Lakes access. This renovated home has 5 bedrooms with 2.5 bathrooms. The renovations include new kitchen cabinets, kitchen appliances and Quartz countertops, fully renovated bathrooms, new flooring, new lighting, new ceiling fans and more. NEW Roof in 2022 and a New Termite bond in 2026! This home also has a newly painted interior/exterior. Winterset Gardens is a highly respected, quaint neighborhood on the shore of Little lake Winterset and offers an optional $100 HOA with a community boat ramp and no deed restrictions allowing direct access to The world renowned Winter Haven Chain of Lakes. 24 canal connected lakes offering great fishing, skiing and leisure boating. Hop on your boat from your neighborhood and go get a bite to eat at several float up bars and restaurants.

6624 Winterset Gardens Road, Winter Haven

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211

$315,000

Welcome to this beautifully maintained 3-bedroom, 2-bathroom home, built in 2020 and located in the gated Lake Deer community. This move-in-ready residence features a bright, open-concept floor plan that seamlessly connects the living room, dining area, and kitchen—ideal for everyday living and entertaining. The kitchen is the heart of the home, offering granite countertops, stainless steel appliances, ample cabinetry, and a spacious center island with additional seating and workspace. Laminate flooring extends throughout the home, providing a clean, modern appearance with no carpet to maintain. The primary suite includes a private bathroom and walk-in closet, while two additional bedrooms are flexibility for guests, a home office, or a personal fitness space. The home also features an attached two-car garage and a covered rear patio overlooking the generously sized backyard—perfect for relaxing, entertaining, or creating your own outdoor retreat. Residents of Lake Deer enjoy access to a community playground and dock for fishing or taking in the peaceful lake views. Additional benefits include low HOA fees, no CDD, and Flood Zone X. Conveniently located near shopping, dining, schools, and major roadways. Schedule your private showing today!

3 Beds ⋅ 2 Baths ⋅ S5158102 MLS

Welcome to this beautifully maintained 3-bedroom, 2-bathroom home, built in 2020 and located in the gated Lake Deer community. This move-in-ready residence features a bright, open-concept floor plan that seamlessly connects the living room, dining area, and kitchen—ideal for everyday living and entertaining. The kitchen is the heart of the home, offering granite countertops, stainless steel appliances, ample cabinetry, and a spacious center island with additional seating and workspace. Laminate flooring extends throughout the home, providing a clean, modern appearance with no carpet to maintain. The primary suite includes a private bathroom and walk-in closet, while two additional bedrooms are flexibility for guests, a home office, or a personal fitness space. The home also features an attached two-car garage and a covered rear patio overlooking the generously sized backyard—perfect for relaxing, entertaining, or creating your own outdoor retreat. Residents of Lake Deer enjoy access to a community playground and dock for fishing or taking in the peaceful lake views. Additional benefits include low HOA fees, no CDD, and Flood Zone X. Conveniently located near shopping, dining, schools, and major roadways. Schedule your private showing today!

195 Black Skimmer Lane, Winter Haven

Listing courtesy of AMY INTERNATIONAL CORP. 407-757-8621

$700,000

NEARLY 5 ACRES | NO HOA | PRIVACY, SPACE & ENDLESS POSSIBILITIES! Welcome to 281 Gerber Dairy Road, where peaceful country-style living meets the convenience of Central Florida! Situated on nearly 5 acres in Winter Haven, this unique property offers the space, privacy, and freedom that can be hard to find. A gated entrance and long private driveway welcome you home, creating a sense of seclusion as you approach this spacious 3-bedroom residence surrounded by beautiful greenery and expansive open space. Whether you're looking for room to spread out, enjoy outdoor hobbies, create beautiful gardens, accommodate recreational equipment, or simply escape the close quarters of traditional neighborhoods, this property offers incredible flexibility. The expansive grounds provide plenty of space for outdoor activities, entertaining, or simply relaxing and enjoying the peaceful surroundings. A detached shed, currently used as a charming "she shed," offers additional space for storage, hobbies, or creative projects. One of the property's standout features is NO HOA! Enjoy the freedom of acreage living without the rules and restrictions of a traditional homeowners association. With nearly 5 acres to make your own, you'll have the opportunity to create an outdoor lifestyle that suits your needs, subject to local zoning and land-use regulations. While the property offers a peaceful, private setting, you're still conveniently located near everything Winter Haven has to offer. Enjoy boating, fishing, and kayaking along the area's famous Chain of Lakes, explore downtown Winter Haven's restaurants, shops, and entertainment, or spend the day at nearby LEGOLAND Florida Resort, Peppa Pig Theme Park, and Bok Tower Gardens. Winter Haven's Central Florida location also provides convenient access to the greater Orlando and Tampa areas. If you've been searching for acreage, privacy, and the freedom to enjoy your property without an HOA, this is an opportunity you won't want to miss. Nearly 5 acres, a gated entrance, and room to make it your own! Schedule your private showing today and discover the possibilities at 281 Gerber Dairy Road!

3 Beds ⋅ 4 Baths ⋅ A4706754 MLS

NEARLY 5 ACRES | NO HOA | PRIVACY, SPACE & ENDLESS POSSIBILITIES! Welcome to 281 Gerber Dairy Road, where peaceful country-style living meets the convenience of Central Florida! Situated on nearly 5 acres in Winter Haven, this unique property offers the space, privacy, and freedom that can be hard to find. A gated entrance and long private driveway welcome you home, creating a sense of seclusion as you approach this spacious 3-bedroom residence surrounded by beautiful greenery and expansive open space. Whether you're looking for room to spread out, enjoy outdoor hobbies, create beautiful gardens, accommodate recreational equipment, or simply escape the close quarters of traditional neighborhoods, this property offers incredible flexibility. The expansive grounds provide plenty of space for outdoor activities, entertaining, or simply relaxing and enjoying the peaceful surroundings. A detached shed, currently used as a charming "she shed," offers additional space for storage, hobbies, or creative projects. One of the property's standout features is NO HOA! Enjoy the freedom of acreage living without the rules and restrictions of a traditional homeowners association. With nearly 5 acres to make your own, you'll have the opportunity to create an outdoor lifestyle that suits your needs, subject to local zoning and land-use regulations. While the property offers a peaceful, private setting, you're still conveniently located near everything Winter Haven has to offer. Enjoy boating, fishing, and kayaking along the area's famous Chain of Lakes, explore downtown Winter Haven's restaurants, shops, and entertainment, or spend the day at nearby LEGOLAND Florida Resort, Peppa Pig Theme Park, and Bok Tower Gardens. Winter Haven's Central Florida location also provides convenient access to the greater Orlando and Tampa areas. If you've been searching for acreage, privacy, and the freedom to enjoy your property without an HOA, this is an opportunity you won't want to miss. Nearly 5 acres, a gated entrance, and room to make it your own! Schedule your private showing today and discover the possibilities at 281 Gerber Dairy Road!

281 Gerber Dairy Road, Winter Haven

Listing courtesy of EXP REALTY LLC. 888-883-8509

$344,900

Welcome to Traditions, a premier 55+ maintenance-free gated community, where resort-style living meets everyday comfort and convenience! This wonderful 2-bedroom, 2-bath home with a den offers Eco Smart construction and an exceptional location just steps from the community clubhouse and directly across the street from the boat ramp. A charming screened-in front entry welcomes you into this beautifully appointed home. Step inside to the spacious Great Room, featuring elegant crown molding and porcelain plank flooring. Oversized glass sliding doors provide an abundance of natural light and open seamlessly to the screened-in lanai, creating an effortless flow between indoor and outdoor living. The gourmet kitchen is truly a chef’s delight, showcasing timeless white shaker cabinetry accented with crown molding and brushed-nickel hardware, complemented by a beautiful glass-tile backsplash. The center island features luxurious quartz countertops and pendant lighting, creating both a stylish focal point and functional workspace. A walk-in pantry and stainless-steel appliance package provide additional convenience and storage. The charming breakfast nook offers the perfect spot for casual dining. Designed for entertaining, the open-concept floor plan allows the formal Dining Room to flow naturally into the Great Room. The versatile Den is an inviting retreat with beautiful views overlooking Lake Ruby, making it an ideal home office, reading room, or additional living space. The Primary Bedroom Suite offers a peaceful retreat, featuring a tray ceiling, wall-to-wall carpeting, and a generously sized walk-in closet. The luxurious Primary Bath features a comfort-height vanity with dual sinks, quartz countertops, private water closet, and a handicapped-accessible tiled shower beautifully finished with decorative Listello tile and glass enclosure. Throughout the home, crown molding and graceful arched entryways add architectural detail and timeless elegance. Step outside to the generously sized screened-in lanai, beautifully finished with pavers and offering a peaceful space to relax, entertain, and enjoy the Florida lifestyle. Additional features include a Laundry Room with cabinetry, washer and dryer, keyless smart-lock entry, smart thermostat, double-pane Low-E windows, AO Smith hybrid water heater, screened front entry, exterior carriage lighting, architectural shingle roof, radiant heat barrier, gutters, exterior stone facade, and paved walkway & driveway. The two-car garage features a garage door opener for added convenience. Traditions offers an exceptional active-adult lifestyle with an impressive array of amenities and planned activities. Residents enjoy a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting room, library, computer room, craft room, dog park, tennis courts, basketball court, bocce, shuffleboard, fitness center, aerobics studio, and so much more. The monthly HOA fee includes lawn service, cable, internet, and exterior house painting, providing added value and making maintenance-free living truly effortless. With its coveted location near the clubhouse and boat ramp, Lake Ruby views, this property offers the perfect combination of resort-style amenities, beautiful surroundings, and everyday convenience.

2 Beds ⋅ 2 Baths ⋅ P4939922 MLS

Welcome to Traditions, a premier 55+ maintenance-free gated community, where resort-style living meets everyday comfort and convenience! This wonderful 2-bedroom, 2-bath home with a den offers Eco Smart construction and an exceptional location just steps from the community clubhouse and directly across the street from the boat ramp. A charming screened-in front entry welcomes you into this beautifully appointed home. Step inside to the spacious Great Room, featuring elegant crown molding and porcelain plank flooring. Oversized glass sliding doors provide an abundance of natural light and open seamlessly to the screened-in lanai, creating an effortless flow between indoor and outdoor living. The gourmet kitchen is truly a chef’s delight, showcasing timeless white shaker cabinetry accented with crown molding and brushed-nickel hardware, complemented by a beautiful glass-tile backsplash. The center island features luxurious quartz countertops and pendant lighting, creating both a stylish focal point and functional workspace. A walk-in pantry and stainless-steel appliance package provide additional convenience and storage. The charming breakfast nook offers the perfect spot for casual dining. Designed for entertaining, the open-concept floor plan allows the formal Dining Room to flow naturally into the Great Room. The versatile Den is an inviting retreat with beautiful views overlooking Lake Ruby, making it an ideal home office, reading room, or additional living space. The Primary Bedroom Suite offers a peaceful retreat, featuring a tray ceiling, wall-to-wall carpeting, and a generously sized walk-in closet. The luxurious Primary Bath features a comfort-height vanity with dual sinks, quartz countertops, private water closet, and a handicapped-accessible tiled shower beautifully finished with decorative Listello tile and glass enclosure. Throughout the home, crown molding and graceful arched entryways add architectural detail and timeless elegance. Step outside to the generously sized screened-in lanai, beautifully finished with pavers and offering a peaceful space to relax, entertain, and enjoy the Florida lifestyle. Additional features include a Laundry Room with cabinetry, washer and dryer, keyless smart-lock entry, smart thermostat, double-pane Low-E windows, AO Smith hybrid water heater, screened front entry, exterior carriage lighting, architectural shingle roof, radiant heat barrier, gutters, exterior stone facade, and paved walkway & driveway. The two-car garage features a garage door opener for added convenience. Traditions offers an exceptional active-adult lifestyle with an impressive array of amenities and planned activities. Residents enjoy a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting room, library, computer room, craft room, dog park, tennis courts, basketball court, bocce, shuffleboard, fitness center, aerobics studio, and so much more. The monthly HOA fee includes lawn service, cable, internet, and exterior house painting, providing added value and making maintenance-free living truly effortless. With its coveted location near the clubhouse and boat ramp, Lake Ruby views, this property offers the perfect combination of resort-style amenities, beautiful surroundings, and everyday convenience.

4075 Bedford Avenue, Winter Haven

Listing courtesy of CENTURY 21 MYERS REALTY LAKE WALES. 863-676-4448

$272,800

Short Sale. Discover modern Florida living in Villamar, a desirable Winter Haven community with peaceful pond views and convenient access to Central Florida attractions. Built in 2024, this single-story 3-bedroom, 2-bath home offers an open-concept layout with spacious living areas, an oversized island, granite countertops, stainless steel appliances, and a pantry. The private primary suite features an ensuite bath, while two additional bedrooms offer flexibility for guests, a home office, or hobbies. Sliding doors open to a relaxing backyard overlooking the pond. Enjoy community amenities including a pool, clubhouse, and playground. Ideally located near US-27 and I-4, with shopping, dining, schools, LEGOLAND Florida Resort, the Winter Haven Chain of Lakes, and Downtown Winter Haven nearby. A wonderful opportunity to make a newer home your own. Short sale.

3 Beds ⋅ 2 Baths ⋅ D6148870 MLS

Short Sale. Discover modern Florida living in Villamar, a desirable Winter Haven community with peaceful pond views and convenient access to Central Florida attractions. Built in 2024, this single-story 3-bedroom, 2-bath home offers an open-concept layout with spacious living areas, an oversized island, granite countertops, stainless steel appliances, and a pantry. The private primary suite features an ensuite bath, while two additional bedrooms offer flexibility for guests, a home office, or hobbies. Sliding doors open to a relaxing backyard overlooking the pond. Enjoy community amenities including a pool, clubhouse, and playground. Ideally located near US-27 and I-4, with shopping, dining, schools, LEGOLAND Florida Resort, the Winter Haven Chain of Lakes, and Downtown Winter Haven nearby. A wonderful opportunity to make a newer home your own. Short sale.

2824 San Marco Way, Winter Haven

Listing courtesy of CENTURY 21 SUNBELT REALTY. 941-235-6610

$269,000

Welcome to this well-maintained 3-bedroom, 2-bath home tucked away on a quiet cul-de-sac. Situated on approximately 0.23 acres, this home features a 2-car garage, vaulted ceilings, upgraded windows, and a bright, comfortable layout. The roof was replaced in November 2021 and the HVAC was replaced in 2022. Interior updates completed in 2024 include new flooring and fresh paint. Master Bedroom has private access to the patio space and an ensuite full bathroom. Enjoy additional living and entertaining space on the screened-in patio with vinyl window coverings.. The property also features an irrigation/sprinkler system. Conveniently located near shopping, dining, schools, and everything the city of Winter Haven provides, this move-in-ready home combines thoughtful updates with a peaceful residential setting. HOA is only $200 annually. Buyer to verify all HOA information, Tax information and Room Dimensions.

3 Beds ⋅ 2 Baths ⋅ L4965239 MLS

Welcome to this well-maintained 3-bedroom, 2-bath home tucked away on a quiet cul-de-sac. Situated on approximately 0.23 acres, this home features a 2-car garage, vaulted ceilings, upgraded windows, and a bright, comfortable layout. The roof was replaced in November 2021 and the HVAC was replaced in 2022. Interior updates completed in 2024 include new flooring and fresh paint. Master Bedroom has private access to the patio space and an ensuite full bathroom. Enjoy additional living and entertaining space on the screened-in patio with vinyl window coverings.. The property also features an irrigation/sprinkler system. Conveniently located near shopping, dining, schools, and everything the city of Winter Haven provides, this move-in-ready home combines thoughtful updates with a peaceful residential setting. HOA is only $200 annually. Buyer to verify all HOA information, Tax information and Room Dimensions.

224 Crown Court, Winter Haven

Listing courtesy of S & D REAL ESTATE SERVICE LLC. 863-824-7169

$169,900

Welcome to this charming 2-bedroom, 1.5-bath manufactured home situated on more than a quarter-acre of owned land with no HOA or lot rent! Located in a quiet, established community, this home offers a spacious, private yard with plenty of room for outdoor entertaining, gardening, pets, or simply enjoying your own peaceful space. The property is comfortable and functional as it stands, while offering an excellent opportunity for someone ready to add a little love, complete a few cosmetic improvements, and make it their own. Recent updates include a remodeled kitchen and septic system, both completed in 2026. The main home features central air conditioning, while the Florida room and detached backyard structure each have mini-split systems. The Florida room provides additional flexible living space, and the separate air-conditioned backyard structure is perfect for a workshop, home office, hobby room, or extra storage. Conveniently located near Cypress Gardens Boulevard, shopping, dining, and LEGOLAND Florida, this property combines privacy, land, flexibility, and value in one unique opportunity.

2 Beds ⋅ 2 Baths ⋅ S5158044 MLS

Welcome to this charming 2-bedroom, 1.5-bath manufactured home situated on more than a quarter-acre of owned land with no HOA or lot rent! Located in a quiet, established community, this home offers a spacious, private yard with plenty of room for outdoor entertaining, gardening, pets, or simply enjoying your own peaceful space. The property is comfortable and functional as it stands, while offering an excellent opportunity for someone ready to add a little love, complete a few cosmetic improvements, and make it their own. Recent updates include a remodeled kitchen and septic system, both completed in 2026. The main home features central air conditioning, while the Florida room and detached backyard structure each have mini-split systems. The Florida room provides additional flexible living space, and the separate air-conditioned backyard structure is perfect for a workshop, home office, hobby room, or extra storage. Conveniently located near Cypress Gardens Boulevard, shopping, dining, and LEGOLAND Florida, this property combines privacy, land, flexibility, and value in one unique opportunity.

5974 Foxhollow Drive, Winter Haven

Listing courtesy of TFP FLORIDA REALTY LLC. 863-337-9667

2437 Crooked Stick, #327 Unit #327, Winter Haven

$79,900

2 Bed | 2 Bath | 1313 sq. ft. | $79,900 | Lot 327 Well kept 1998 Home of Merit manufactured home in gated Four Lakes Golf Community. This is a great home for a very low price in Four Lakes. The home is partially furnished with new windows and a 2022 air conditioner. This home has views of the golf course from the lanai and has a separate patio. The driveway has been resurfaced. This home has an updated beautiful shower in the master bath and the bedrooms have very large closets. At the rear of the home there is a large windowed lanai that showcases golf course views. The home comes with a newer golf cart which has new batteries and a new charger and will come with one year free golf.

2 Beds ⋅ 2 Baths ⋅ 11915800 MLS

2 Bed | 2 Bath | 1313 sq. ft. | $79,900 | Lot 327 Well kept 1998 Home of Merit manufactured home in gated Four Lakes Golf Community. This is a great home for a very low price in Four Lakes. The home is partially furnished with new windows and a 2022 air conditioner. This home has views of the golf course from the lanai and has a separate patio. The driveway has been resurfaced. This home has an updated beautiful shower in the master bath and the bedrooms have very large closets. At the rear of the home there is a large windowed lanai that showcases golf course views. The home comes with a newer golf cart which has new batteries and a new charger and will come with one year free golf.

2437 Crooked Stick, #327 Unit #327, Winter Haven

Listing courtesy of Cheryl Dobbs with CRF Communities

$255,000

Move right into this lovingly maintained 3-bedroom, 2-bath home with a 2-car garage nestled in Eagle Landing. Low annual HOA fee. Spanning nearly 1,300 square feet of living space, this home features a bright and airy open floor plan that effortlessly connects the living, dining, and kitchen areas. The kitchen showcases beautiful countertops, ample cabinetry, a close pantry, and a functional island. The primary bedroom is complete with a walk-in closet and its own bathroom. The additional bedrooms provide plenty of versatility for family, guests, or a dedicated home office. Enjoy the ease of a dedicated indoor laundry room. Step outside to a rear covered porch overlooking a fully fenced-in backyard, ideal for relaxation, pets, play, and outdoor gatherings. Don't delay; call and schedule your appointment today.

3 Beds ⋅ 2 Baths ⋅ P4939942 MLS

Move right into this lovingly maintained 3-bedroom, 2-bath home with a 2-car garage nestled in Eagle Landing. Low annual HOA fee. Spanning nearly 1,300 square feet of living space, this home features a bright and airy open floor plan that effortlessly connects the living, dining, and kitchen areas. The kitchen showcases beautiful countertops, ample cabinetry, a close pantry, and a functional island. The primary bedroom is complete with a walk-in closet and its own bathroom. The additional bedrooms provide plenty of versatility for family, guests, or a dedicated home office. Enjoy the ease of a dedicated indoor laundry room. Step outside to a rear covered porch overlooking a fully fenced-in backyard, ideal for relaxation, pets, play, and outdoor gatherings. Don't delay; call and schedule your appointment today.

813 Eagle Rock Ter, Winter Haven

Listing courtesy of ASSOCIATE REALTY. 863-618-4000

$420,000

Welcome to 900 Lake Martha Drive NE, a truly unique lakefront property offering exceptional space, flexibility, and endless possibilities! The property extends across the street to Lake Martha, providing direct lake frontage and wonderful opportunities to enjoy the waterfront. Information provided by the City, the lakefront portion may be divided from the main homesite, creating even more possibilities for the property. The main portion of the home features three bedrooms and two bathrooms, spacious living and dining areas, and a large bonus room currently used as a pool and game room. This flexible space could also serve as a family room, home office, gym, or additional entertainment area. Located on the opposite side of the home, the private in-law suite offers separation from the main living area, its own entrance, and a full bathroom. Above the two-car garage is an expansive room with a full bathroom and space for a kitchenette. This versatile area could become a movie room, game room, additional primary suite, guest quarters, or a second in-law suite. The garage also includes an additional shower—perfect for rinsing off after boating, fishing, yardwork, or a day by the lake. Enjoy Florida living from the screened front and rear porches. The fenced side yard is already improved with crushed gravel, providing convenient parking for a boat, RV, trailer, or other recreational vehicles. With direct lake frontage, multiple living areas, flexible bonus spaces, and the potential to separate the waterfront portion, this property offers outstanding possibilities for multigenerational living, extended-family accommodations, guest quarters, or potential short- or long-term rental use. Bring your ideas and discover everything this one-of-a-kind Lake Martha property has to offer!

4 Beds ⋅ 4 Baths ⋅ L4965109 MLS

Welcome to 900 Lake Martha Drive NE, a truly unique lakefront property offering exceptional space, flexibility, and endless possibilities! The property extends across the street to Lake Martha, providing direct lake frontage and wonderful opportunities to enjoy the waterfront. Information provided by the City, the lakefront portion may be divided from the main homesite, creating even more possibilities for the property. The main portion of the home features three bedrooms and two bathrooms, spacious living and dining areas, and a large bonus room currently used as a pool and game room. This flexible space could also serve as a family room, home office, gym, or additional entertainment area. Located on the opposite side of the home, the private in-law suite offers separation from the main living area, its own entrance, and a full bathroom. Above the two-car garage is an expansive room with a full bathroom and space for a kitchenette. This versatile area could become a movie room, game room, additional primary suite, guest quarters, or a second in-law suite. The garage also includes an additional shower—perfect for rinsing off after boating, fishing, yardwork, or a day by the lake. Enjoy Florida living from the screened front and rear porches. The fenced side yard is already improved with crushed gravel, providing convenient parking for a boat, RV, trailer, or other recreational vehicles. With direct lake frontage, multiple living areas, flexible bonus spaces, and the potential to separate the waterfront portion, this property offers outstanding possibilities for multigenerational living, extended-family accommodations, guest quarters, or potential short- or long-term rental use. Bring your ideas and discover everything this one-of-a-kind Lake Martha property has to offer!

900 Lake Martha Drive Ne, Winter Haven

Listing courtesy of KELLER WILLIAMS REALTY SMART 1. 863-508-3000

$340,000

** $10K PRICE REDUCTION as of 10/23/2026!!** More space, more flexibility, and more included! Located near LEGOLAND Florida Resort, this spacious Winter Haven home offers 2,257 square feet of total living area, including a permitted 320-square-foot addition completed in 2021. The interior features a bright main living area with vaulted ceilings, a separate dining space, generously sized bedrooms, an interior laundry room, and a well-equipped kitchen with ample cabinetry and counter space. The refrigerator, range, microwave, dishwasher, washer, and dryer are all included. Step outside to a fenced backyard designed for enjoying the Florida lifestyle. A brand-new permitted covered patio, completed in March 2026, provides an inviting shaded space for relaxing, grilling, or entertaining. The backyard also features mature shade trees and a paver gathering area with a built-in firepit and seating. Additional highlights include a complete HVAC system installed in 2023, a main house roof installed in 2017, a new patio roof installed in 2026, a two-car garage, an included security system, and eight included 360-degree security cameras. Conveniently positioned in Central Florida between Orlando and Tampa, the home provides access to major attractions, shopping, dining, recreation, and everything the Winter Haven area has to provide. With substantial living space, valuable permitted improvements, included appliances, and an outdoor area ready to enjoy, this home delivers features that are increasingly difficult to find at this price point. Schedule your private showing and see how much this property has to give.

4 Beds ⋅ 2 Baths ⋅ L4965212 MLS

** $10K PRICE REDUCTION as of 10/23/2026!!** More space, more flexibility, and more included! Located near LEGOLAND Florida Resort, this spacious Winter Haven home offers 2,257 square feet of total living area, including a permitted 320-square-foot addition completed in 2021. The interior features a bright main living area with vaulted ceilings, a separate dining space, generously sized bedrooms, an interior laundry room, and a well-equipped kitchen with ample cabinetry and counter space. The refrigerator, range, microwave, dishwasher, washer, and dryer are all included. Step outside to a fenced backyard designed for enjoying the Florida lifestyle. A brand-new permitted covered patio, completed in March 2026, provides an inviting shaded space for relaxing, grilling, or entertaining. The backyard also features mature shade trees and a paver gathering area with a built-in firepit and seating. Additional highlights include a complete HVAC system installed in 2023, a main house roof installed in 2017, a new patio roof installed in 2026, a two-car garage, an included security system, and eight included 360-degree security cameras. Conveniently positioned in Central Florida between Orlando and Tampa, the home provides access to major attractions, shopping, dining, recreation, and everything the Winter Haven area has to provide. With substantial living space, valuable permitted improvements, included appliances, and an outdoor area ready to enjoy, this home delivers features that are increasingly difficult to find at this price point. Schedule your private showing and see how much this property has to give.

817 Reflections Loop E, Winter Haven

Listing courtesy of KELLER WILLIAMS REALTY SMART 1. 863-508-3000

$1,200

Super cozy 1/1 home! Enjoy this opportunity, call today!

1 Beds ⋅ 1 Baths ⋅ 11994346 MLS

Super cozy 1/1 home! Enjoy this opportunity, call today!

723 24th Street Nw, Winter Haven

Listing courtesy of Valentina Vakhova with Maktub Realty

$237,900

One or more photos have been virtually staged Charming 3/2 in Cypress Landings on Lake Dexter! Welcome home to this adorable 3-bedroom, 2-bath property located in the highly desirable Cypress Landings community on beautiful Lake Dexter. Step inside to an inviting open floor plan featuring cathedral ceilings that make the living space feel bright, airy, and perfect for everyday living or entertaining. The large primary bedroom offers plenty of comfort with its walkin closet and a private ensuite bath complete with a convenient step in shower. Living in Cypress Landings means enjoying a lifestyle full of amenities, including: Community boat ramp, Fishing pier, Clubhouse, Heated pool, Tennis courts. All of this, plus a location that keeps you close to shopping, medical offices, dining, and more. This community does not allow short term rentals, ensuring a peaceful, residential atmosphere. A wonderful opportunity to enjoy lake access, great amenities, and a cozy home in a fantastic Winter Haven neighborhood!

3 Beds ⋅ 2 Baths ⋅ P4939927 MLS

One or more photos have been virtually staged Charming 3/2 in Cypress Landings on Lake Dexter! Welcome home to this adorable 3-bedroom, 2-bath property located in the highly desirable Cypress Landings community on beautiful Lake Dexter. Step inside to an inviting open floor plan featuring cathedral ceilings that make the living space feel bright, airy, and perfect for everyday living or entertaining. The large primary bedroom offers plenty of comfort with its walkin closet and a private ensuite bath complete with a convenient step in shower. Living in Cypress Landings means enjoying a lifestyle full of amenities, including: Community boat ramp, Fishing pier, Clubhouse, Heated pool, Tennis courts. All of this, plus a location that keeps you close to shopping, medical offices, dining, and more. This community does not allow short term rentals, ensuring a peaceful, residential atmosphere. A wonderful opportunity to enjoy lake access, great amenities, and a cozy home in a fantastic Winter Haven neighborhood!

4116 Fishermans Landing, Winter Haven

Listing courtesy of STACEY TOWNS REALTY LLC. 863-422-1585

$189,000

Unique opportunity to purchase a home with TWO additional contiguous parcels — THREE parcels offered together for a total package price of $199,000! 134 Lichtenwalter Rd – $199,000 1500 Gaines Rd – (PID) 25-29-11-000000-023360 0 Gaines Rd – (PID) 25-29-11-000000-023520 134 Lichtenwalter Rd features a 2020 manufactured home offering 3 bedrooms, 2 bathrooms, and approximately 1,080 sq. ft. of living space. Adding even more potential, 1500 Gaines Rd has an existing setup previously intended for a second mobile home, including its own electrical pole. The additional parcels provide extra space, privacy, and possibilities for future use. All three parcels are being offered together for $199,000. A great opportunity for buyers looking for a home with additional land and flexibility! Buyer and buyer’s agent are responsible for verifying zoning, utilities, permitting, impact fees, and whether an additional manufactured/mobile home may be placed on the property with the appropriate governmental authorities.

3 Beds ⋅ 2 Baths ⋅ TB8550554 MLS

Unique opportunity to purchase a home with TWO additional contiguous parcels — THREE parcels offered together for a total package price of $199,000! 134 Lichtenwalter Rd – $199,000 1500 Gaines Rd – (PID) 25-29-11-000000-023360 0 Gaines Rd – (PID) 25-29-11-000000-023520 134 Lichtenwalter Rd features a 2020 manufactured home offering 3 bedrooms, 2 bathrooms, and approximately 1,080 sq. ft. of living space. Adding even more potential, 1500 Gaines Rd has an existing setup previously intended for a second mobile home, including its own electrical pole. The additional parcels provide extra space, privacy, and possibilities for future use. All three parcels are being offered together for $199,000. A great opportunity for buyers looking for a home with additional land and flexibility! Buyer and buyer’s agent are responsible for verifying zoning, utilities, permitting, impact fees, and whether an additional manufactured/mobile home may be placed on the property with the appropriate governmental authorities.

134 Lichtenwalter Road, Winter Haven

Listing courtesy of ELEVE REAL ESTATE LLC. 407-743-7472

$430,000

A Dream come true in Winter Haven! This beautiful 4-bedroom, 2-bath home checks all the boxes: NO HOA, a private pool, and a spacious backyard. Enjoy comfortable indoor living and plenty of outdoor space to relax and entertain. Conveniently located in the Cypress Gardens area near LEGOLAND Florida, shopping, dining, and everyday conveniences. A wonderful combination of space, freedom, location, and Florida lifestyle. Schedule your private showing today!

4 Beds ⋅ 2 Baths ⋅ S5157963 MLS

A Dream come true in Winter Haven! This beautiful 4-bedroom, 2-bath home checks all the boxes: NO HOA, a private pool, and a spacious backyard. Enjoy comfortable indoor living and plenty of outdoor space to relax and entertain. Conveniently located in the Cypress Gardens area near LEGOLAND Florida, shopping, dining, and everyday conveniences. A wonderful combination of space, freedom, location, and Florida lifestyle. Schedule your private showing today!

9 Winterset Dr, Winter Haven

Listing courtesy of LPT REALTY, LLC. 877-366-2213

$210,000

Discover this traditional 2-bedroom, 2-bath villa offering a bright, open layout and exceptional pride of ownership throughout. The welcoming foyer with a cozy sitting area leads into a spacious great room and dining area overlooking the enclosed Florida room and serene garden courtyard. The well-appointed kitchen features abundant cabinetry, a closet pantry, and an open design perfect for entertaining. Both bedrooms are generously sized with ample closet space. Home has garage door screen, flagstone patio with tropical plantings, and a roof replaced in 2013/2014. Located in the desirable Park Lake community, residents enjoy a large pool, recreational building, private dock on the renowned Chain of Lakes, and plentiful guest parking. Ideally situated near shopping, medical facilities, restaurants, downtown attractions, and the bus line, this beautifully maintained villa offers comfort, convenience, and a relaxing Florida lifestyle.

2 Beds ⋅ 2 Baths ⋅ L4964845 MLS

Discover this traditional 2-bedroom, 2-bath villa offering a bright, open layout and exceptional pride of ownership throughout. The welcoming foyer with a cozy sitting area leads into a spacious great room and dining area overlooking the enclosed Florida room and serene garden courtyard. The well-appointed kitchen features abundant cabinetry, a closet pantry, and an open design perfect for entertaining. Both bedrooms are generously sized with ample closet space. Home has garage door screen, flagstone patio with tropical plantings, and a roof replaced in 2013/2014. Located in the desirable Park Lake community, residents enjoy a large pool, recreational building, private dock on the renowned Chain of Lakes, and plentiful guest parking. Ideally situated near shopping, medical facilities, restaurants, downtown attractions, and the bus line, this beautifully maintained villa offers comfort, convenience, and a relaxing Florida lifestyle.

2206 San Marcos Circle Se, Winter Haven

Listing courtesy of COLDWELL BANKER REALTY. 863-294-7541

$409,000

Discover your own private Florida retreat in this stunning 3-bedroom, 2.5-bathroom pool home, built in 2018 and offering over 2,600 square feet of living space on a spacious, nearly quarter-acre lot in Winter Haven, Florida! Designed for comfort, entertaining, and everyday living, this beautiful two-story residence features an expansive floor plan with a generously sized primary suite, an oversized walk-in closet, and a huge upstairs loft offering endless possibilities for a home office, media room, game room, or additional living area. The heart of the home is the spacious kitchen, featuring elegant quartz countertops, a large center island, abundant cabinetry, and plenty of room for preparing meals and gathering with guests. Step outside into your very own backyard paradise! Enjoy a gorgeous screened-in private swimming pool surrounded by an elegant travertine pool deck, all within a fully fenced backyard offering privacy and plenty of outdoor space. Whether you're hosting weekend gatherings, relaxing poolside, or enjoying Florida's year-round sunshine, this outdoor retreat is designed to impress. Additional highlights include a two-car garage, an extended driveway providing ample parking, and access to a community swimming pool. Located in the desirable Lake Lucerne community, this home offers convenient access to US Highway 27, Interstate 4, shopping, dining, and everyday essentials. Enjoy the attractions of Central Florida, including LEGOLAND Florida Resort, Winter Haven's famous Chain of Lakes, nearby parks, and the restaurants and entertainment of Downtown Winter Haven. The location also provides convenient connections to Haines City, Davenport, and the greater Orlando area. Why settle for an ordinary home when you can enjoy your own private pool, an oversized primary suite, generous living space, and an exceptional Central Florida location? Schedule your private showing today and experience everything this Winter Haven pool home has to offer!

3 Beds ⋅ 3 Baths ⋅ S5157925 MLS

Discover your own private Florida retreat in this stunning 3-bedroom, 2.5-bathroom pool home, built in 2018 and offering over 2,600 square feet of living space on a spacious, nearly quarter-acre lot in Winter Haven, Florida! Designed for comfort, entertaining, and everyday living, this beautiful two-story residence features an expansive floor plan with a generously sized primary suite, an oversized walk-in closet, and a huge upstairs loft offering endless possibilities for a home office, media room, game room, or additional living area. The heart of the home is the spacious kitchen, featuring elegant quartz countertops, a large center island, abundant cabinetry, and plenty of room for preparing meals and gathering with guests. Step outside into your very own backyard paradise! Enjoy a gorgeous screened-in private swimming pool surrounded by an elegant travertine pool deck, all within a fully fenced backyard offering privacy and plenty of outdoor space. Whether you're hosting weekend gatherings, relaxing poolside, or enjoying Florida's year-round sunshine, this outdoor retreat is designed to impress. Additional highlights include a two-car garage, an extended driveway providing ample parking, and access to a community swimming pool. Located in the desirable Lake Lucerne community, this home offers convenient access to US Highway 27, Interstate 4, shopping, dining, and everyday essentials. Enjoy the attractions of Central Florida, including LEGOLAND Florida Resort, Winter Haven's famous Chain of Lakes, nearby parks, and the restaurants and entertainment of Downtown Winter Haven. The location also provides convenient connections to Haines City, Davenport, and the greater Orlando area. Why settle for an ordinary home when you can enjoy your own private pool, an oversized primary suite, generous living space, and an exceptional Central Florida location? Schedule your private showing today and experience everything this Winter Haven pool home has to offer!

119 Sunfish Drive, Winter Haven

Listing courtesy of EXIT REALTY 4CORNERS. 863-344-3948

$145,997

2 Lots, 1 Home, and an Oversized Workshop – Endless Potential in Winter Haven! Attention investors, builders, and buyers looking for value and versatility! This unique multi-lot package includes two adjacent parcels offering flexibility, space, and immediate upside. 215 10th Wahneta St W (Parcel 1): Features a 2-bedroom, 1-bathroom single-family home in need of TLC, offering a solid blank canvas for a value-add flip, long-term rental, or primary residence. 213 10th Wahneta St W (Parcel 2): Cleared and ready lot featuring a standalone 480 sq. ft. detached workshop/garage—ideal for extra storage, equipment, workspace, or potential future development. The grounds have been freshly cleaned up, making site evaluation simple and straightforward. Whether you're looking to renovate the existing home and keep the second lot for private workspace/storage, explore future building opportunities, or create an income-generating property, this rare two-lot setup at an accessible price point is a standout investment opportunity. Don't miss out—schedule your showing today!

2 Beds ⋅ 1 Baths ⋅ P4939902 MLS

2 Lots, 1 Home, and an Oversized Workshop – Endless Potential in Winter Haven! Attention investors, builders, and buyers looking for value and versatility! This unique multi-lot package includes two adjacent parcels offering flexibility, space, and immediate upside. 215 10th Wahneta St W (Parcel 1): Features a 2-bedroom, 1-bathroom single-family home in need of TLC, offering a solid blank canvas for a value-add flip, long-term rental, or primary residence. 213 10th Wahneta St W (Parcel 2): Cleared and ready lot featuring a standalone 480 sq. ft. detached workshop/garage—ideal for extra storage, equipment, workspace, or potential future development. The grounds have been freshly cleaned up, making site evaluation simple and straightforward. Whether you're looking to renovate the existing home and keep the second lot for private workspace/storage, explore future building opportunities, or create an income-generating property, this rare two-lot setup at an accessible price point is a standout investment opportunity. Don't miss out—schedule your showing today!

213 10th Wahneta Street W, Winter Haven

Listing courtesy of J&T PROPERTY SOLUTIONS GROUP LLC. 863-440-3603

$259,000

Virtually Staged. UPDATED 4-BEDROOM, 3-BATH HOME WITH FLEXIBLE IN-LAW SUITE IN WINTER HAVEN! Welcome home to this nicely updated and versatile 4-bedroom, 3-bathroom property in the heart of Winter Haven! With major components already updated—including the septic drain field (2026), plumbing, AC and duct work (2025) and roof (2023) and updated current FHA tie down compliant!—this home offers a great combination of comfort, flexibility, and functionality. Step inside to a spacious living room and dining room combination, with fresh paint and new flooring throughout. The split-bedroom floor plan provides privacy and features generously sized bedrooms with walk-in closets. The primary suite offers plenty of space and a large ensuite bathroom. One of the home's standout features is the one-bedroom, one-bath in-law/guest suite, complete with a separate entrance and conveniently separated from the main living area by a hallway. This flexible space can accommodate a variety of needs, whether used for extended family, guests, a home office, workshop, craft room, or other personal space. The layout also offers the potential to add a small kitchenette for even greater functionality. Additional updates include updated bathrooms and a convenient indoor laundry area tucked behind the kitchen. Step outside to the spacious backyard, offering plenty of room for entertaining, relaxing, gardening, or enjoying the Florida sunshine. For outdoor enthusiasts, a community boat ramp to Lake Fox is just around the corner. Not in a flood zone and not in an HOA!The home is also conveniently located near schools, shopping, healthcare, and LEGOLAND Florida. With its flexible floor plan, major updates, spacious yard, and desirable location, this home offers plenty of possibilities for a homeowner or investor. Schedule your private showing today and come see all this property has to offer!

4 Beds ⋅ 3 Baths ⋅ P4939940 MLS

Virtually Staged. UPDATED 4-BEDROOM, 3-BATH HOME WITH FLEXIBLE IN-LAW SUITE IN WINTER HAVEN! Welcome home to this nicely updated and versatile 4-bedroom, 3-bathroom property in the heart of Winter Haven! With major components already updated—including the septic drain field (2026), plumbing, AC and duct work (2025) and roof (2023) and updated current FHA tie down compliant!—this home offers a great combination of comfort, flexibility, and functionality. Step inside to a spacious living room and dining room combination, with fresh paint and new flooring throughout. The split-bedroom floor plan provides privacy and features generously sized bedrooms with walk-in closets. The primary suite offers plenty of space and a large ensuite bathroom. One of the home's standout features is the one-bedroom, one-bath in-law/guest suite, complete with a separate entrance and conveniently separated from the main living area by a hallway. This flexible space can accommodate a variety of needs, whether used for extended family, guests, a home office, workshop, craft room, or other personal space. The layout also offers the potential to add a small kitchenette for even greater functionality. Additional updates include updated bathrooms and a convenient indoor laundry area tucked behind the kitchen. Step outside to the spacious backyard, offering plenty of room for entertaining, relaxing, gardening, or enjoying the Florida sunshine. For outdoor enthusiasts, a community boat ramp to Lake Fox is just around the corner. Not in a flood zone and not in an HOA!The home is also conveniently located near schools, shopping, healthcare, and LEGOLAND Florida. With its flexible floor plan, major updates, spacious yard, and desirable location, this home offers plenty of possibilities for a homeowner or investor. Schedule your private showing today and come see all this property has to offer!

5707 E Lake Fox Drive, Winter Haven

Listing courtesy of COLDWELL BANKER REALTY. 863-294-7541

$134,900

Welcome to Cypress Creek Village in Winter Haven, an active and friendly 55-plus gated community where Winter Haven is truly the place to be, with a low monthly lot rent of only $690.23. This 2020 Mandy model offers two bedrooms, two full master suites, and extensive custom upgrades throughout. Outside features an expansive covered carport alongside a decorative epoxy concrete driveway and pathway leading directly to the rear of the property. The exterior includes dedicated golf cart parking paired with a golf cart garage or storage shed. Enter inside to an open living area and kitchen finished with durable vinyl plank flooring, crown-molded ceilings, and plush carpeting in each bedroom. The kitchen is outfitted with 36-inch solid cabinetry, stainless steel appliances, and a classic farmhouse sink. A separate, dedicated laundry room provides added everyday convenience. Outdoor living includes an oversized lanai and an adjoining screened porch providing direct pond views. Cypress Creek Village amenities include a central clubhouse, swimming pool, hot tub and jacuzzi, fitness center, billiards room, library, pickleball courts, shuffleboard, horseshoe pits, and a private movie theater complete with fresh popcorn. The pet-friendly community is located minutes from local restaurants, LEGOLAND Florida, and championship golf across Dundee Road at Cypresswood Golf and Country Club. This home is absolutely beautiful. Schedule a showing today and make this dream home your reality.

2 Beds ⋅ 2 Baths ⋅ 11986655 MLS

Welcome to Cypress Creek Village in Winter Haven, an active and friendly 55-plus gated community where Winter Haven is truly the place to be, with a low monthly lot rent of only $690.23. This 2020 Mandy model offers two bedrooms, two full master suites, and extensive custom upgrades throughout. Outside features an expansive covered carport alongside a decorative epoxy concrete driveway and pathway leading directly to the rear of the property. The exterior includes dedicated golf cart parking paired with a golf cart garage or storage shed. Enter inside to an open living area and kitchen finished with durable vinyl plank flooring, crown-molded ceilings, and plush carpeting in each bedroom. The kitchen is outfitted with 36-inch solid cabinetry, stainless steel appliances, and a classic farmhouse sink. A separate, dedicated laundry room provides added everyday convenience. Outdoor living includes an oversized lanai and an adjoining screened porch providing direct pond views. Cypress Creek Village amenities include a central clubhouse, swimming pool, hot tub and jacuzzi, fitness center, billiards room, library, pickleball courts, shuffleboard, horseshoe pits, and a private movie theater complete with fresh popcorn. The pet-friendly community is located minutes from local restaurants, LEGOLAND Florida, and championship golf across Dundee Road at Cypresswood Golf and Country Club. This home is absolutely beautiful. Schedule a showing today and make this dream home your reality.

1201 Cypress Vine Road, Winter Haven

Listing courtesy of Lisa Dobbs with LISA DOBBS LLC

$349,000

Space, a Screened Pool and a location that keeps you connected! This 4-bedroom, 2.5-bath pool home on the north side of Winter Haven offers 2,836 sqft, a first-floor office/den, an upstairs bonus room and a 2-car garage. The HOA is only $350 a year, there's NO CDD, and it's in Flood Zone X. Out back, the screen enclosure covers both the 24x14 in-ground pool and the 38x11 covered lanai with ceiling fans, giving you a shaded spot to dine, relax or entertain any time of year. Past the pool, the backyard has room for pets, gardening or play. Inside, high ceilings and ceiling fans keep things bright and open. The kitchen opens to the family room and has granite counters, a cooking island, dual sinks and two pantries, with a separate dining room nearby. The 13x13 den works well as a home office, playroom or guest space. Upstairs, the bonus room sits at the center of the bedroom hallways and makes a great media room, hangout or second office. The 19x16 primary suite has two walk-in closets and an en suite bath with granite counters, a vanity area, a garden tub, a separate shower, a private toilet room and a linen closet. Three more bedrooms, including a roomy 16x13, share a second full bath with dual sinks. Roof was replaced in 2022 and the downstairs HVAC was replaced in 2026. The washer, dryer, refrigerator, range, dishwasher and microwave all stay, and there's an inside laundry room. Furnishings are negotiable. Quick access to SR 27 puts Haines City, Davenport and I-4 within easy reach for commuting toward Orlando or Tampa.

4 Beds ⋅ 3 Baths ⋅ P4939913 MLS

Space, a Screened Pool and a location that keeps you connected! This 4-bedroom, 2.5-bath pool home on the north side of Winter Haven offers 2,836 sqft, a first-floor office/den, an upstairs bonus room and a 2-car garage. The HOA is only $350 a year, there's NO CDD, and it's in Flood Zone X. Out back, the screen enclosure covers both the 24x14 in-ground pool and the 38x11 covered lanai with ceiling fans, giving you a shaded spot to dine, relax or entertain any time of year. Past the pool, the backyard has room for pets, gardening or play. Inside, high ceilings and ceiling fans keep things bright and open. The kitchen opens to the family room and has granite counters, a cooking island, dual sinks and two pantries, with a separate dining room nearby. The 13x13 den works well as a home office, playroom or guest space. Upstairs, the bonus room sits at the center of the bedroom hallways and makes a great media room, hangout or second office. The 19x16 primary suite has two walk-in closets and an en suite bath with granite counters, a vanity area, a garden tub, a separate shower, a private toilet room and a linen closet. Three more bedrooms, including a roomy 16x13, share a second full bath with dual sinks. Roof was replaced in 2022 and the downstairs HVAC was replaced in 2026. The washer, dryer, refrigerator, range, dishwasher and microwave all stay, and there's an inside laundry room. Furnishings are negotiable. Quick access to SR 27 puts Haines City, Davenport and I-4 within easy reach for commuting toward Orlando or Tampa.

5809 Windridge Drive, Winter Haven

Listing courtesy of CROSBY & ASSOCIATES, INC.. 863-293-5600

$319,999

Welcome to this beautifully designed 4 bedroom, 2.5 bathroom two-story home, built in 2024, offering modern style, thoughtful upgrades, and easy maintenance living. Step inside to discover elegant tile flooring throughout the main level, creating a sleek and inviting atmosphere. The spacious kitchen features stunning quartz countertops, upgraded appliances, and beautiful gold accents that add a touch of sophistication to the heart of the home. Upstairs, you’ll find comfortable bedrooms with plush carpeting, including a spacious primary suite designed for relaxation. The open concept layout provides plenty of space for entertaining, everyday living, and making lasting memories. Step outside to enjoy the large paved backyard area, perfect for outdoor dining, entertaining, or creating your own private retreat. The backyard also features turf instead of traditional grass, providing a beautiful, low maintenance outdoor space without the hassle of regular mowing and upkeep. This move in ready home offers the perfect combination of comfort, style, and convenience.

4 Beds ⋅ 3 Baths ⋅ O6443234 MLS

Welcome to this beautifully designed 4 bedroom, 2.5 bathroom two-story home, built in 2024, offering modern style, thoughtful upgrades, and easy maintenance living. Step inside to discover elegant tile flooring throughout the main level, creating a sleek and inviting atmosphere. The spacious kitchen features stunning quartz countertops, upgraded appliances, and beautiful gold accents that add a touch of sophistication to the heart of the home. Upstairs, you’ll find comfortable bedrooms with plush carpeting, including a spacious primary suite designed for relaxation. The open concept layout provides plenty of space for entertaining, everyday living, and making lasting memories. Step outside to enjoy the large paved backyard area, perfect for outdoor dining, entertaining, or creating your own private retreat. The backyard also features turf instead of traditional grass, providing a beautiful, low maintenance outdoor space without the hassle of regular mowing and upkeep. This move in ready home offers the perfect combination of comfort, style, and convenience.

231 Hayley Street, Winter Haven

Listing courtesy of RE/MAX ASSURED. 800-393-8600

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